(2-benzyloxycarbonylaminoethyl)phosphonic acid benzyl ester | 88981-21-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2-benzyloxycarbonylaminoethyl)phosphonic acid benzyl ester
• 英文别名: Cbz-Aep(OBzl)(OH)；2-(N-benzyloxycarbonylamino)ethylphosphonic acid benzyl ester；phenylmethoxy-[2-(phenylmethoxycarbonylamino)ethyl]phosphinic acid
• CAS: 88981-21-9
• 化学式: C₁₇H₂₀NO₅P
• 分子量: 349.323
• InChiKey: BGAQRSGLXDQYTR-UHFFFAOYSA-N

物化性质

• 熔点：
  130-132 °C(Solv: acetone (67-64-1))
• 密度：
  1.280±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.32
• 重原子数：
  24.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  84.86
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2-benzyloxycarbonylaminoethyl)phosphonic acid benzyl ester 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 benzyl N-[2-(chloro-oxido-phenylmethoxyphosphaniumyl)ethyl]carbamate
  参考文献：
  名称：

  Synthesis of the Core Tetrasaccharide of Trypanosoma cruzi Glycoinositolphospholipids: Manp(α1→6)-Manp(α1→4)-6-(2-aminoethylphosphonic acid)-GlcNp(α1→6)-myo-Ins-1-PO₄

  摘要：

  Synthesis of the core tetrasaccharide Manp(alpha 1 -> 6)-Manp((alpha 1 -> 4)-6-(2-aminoethylphosphonic acid)GlcNp((alpha 1 -> 6)-myo-Ins-1-PO4, found in glycoinositolphospholipids of Trypanosoma cruzi parasites, is described. The key building block, 6-0-(2-azido-3-0-benzyl-6-0-((2-benzyloxycarbonylaminoethyl)phosphonic acid benzyl ester)-2-deoxy-alpha-D-glueopyranosyl)-1-di-O-benzylphosphoryl-4,5-O-isopropylidene-2,3-O-(D-1,7,7-trimethyl[2,2,1]bicyclohept-6-ylidene)-D-Myo-inositol, was synthesized using a partially protected glucosyl D-camphorinositolphosphate and a (2-benzyloxycarbonylaminoethyl)phosphonic acid derivative in a regioselective phosphonate esterfication. Elongation with ethyl 2-O-benzoyl-3,4,6-tri-O-benzyl-alpha-D-mannopyranosyl-(1 -> 6)-2,3,4-tri-O-benzyl-l-alpha-D-thiomannopyrano- side using dimethyl(methylthio)sulfonium trifluoromethanesulfonate gave A fully protected tetrasaccharide which was successfully deprotected subsequently with sodium methoxide, sodium in liquid ammonia, and aq hydrochloric acid to give title compound.

  DOI：

  10.1021/jo0508595
• 作为产物：
  描述：

  在 盐酸 作用下， 反应 0.5h， 以1.07 g的产率得到(2-benzyloxycarbonylaminoethyl)phosphonic acid benzyl ester
  参考文献：
  名称：

  Synthesis of the Core Tetrasaccharide of Trypanosoma cruzi Glycoinositolphospholipids: Manp(α1→6)-Manp(α1→4)-6-(2-aminoethylphosphonic acid)-GlcNp(α1→6)-myo-Ins-1-PO₄

  摘要：

  Synthesis of the core tetrasaccharide Manp(alpha 1 -> 6)-Manp((alpha 1 -> 4)-6-(2-aminoethylphosphonic acid)GlcNp((alpha 1 -> 6)-myo-Ins-1-PO4, found in glycoinositolphospholipids of Trypanosoma cruzi parasites, is described. The key building block, 6-0-(2-azido-3-0-benzyl-6-0-((2-benzyloxycarbonylaminoethyl)phosphonic acid benzyl ester)-2-deoxy-alpha-D-glueopyranosyl)-1-di-O-benzylphosphoryl-4,5-O-isopropylidene-2,3-O-(D-1,7,7-trimethyl[2,2,1]bicyclohept-6-ylidene)-D-Myo-inositol, was synthesized using a partially protected glucosyl D-camphorinositolphosphate and a (2-benzyloxycarbonylaminoethyl)phosphonic acid derivative in a regioselective phosphonate esterfication. Elongation with ethyl 2-O-benzoyl-3,4,6-tri-O-benzyl-alpha-D-mannopyranosyl-(1 -> 6)-2,3,4-tri-O-benzyl-l-alpha-D-thiomannopyrano- side using dimethyl(methylthio)sulfonium trifluoromethanesulfonate gave A fully protected tetrasaccharide which was successfully deprotected subsequently with sodium methoxide, sodium in liquid ammonia, and aq hydrochloric acid to give title compound.

  DOI：

  10.1021/jo0508595

文献信息

• Synthesis of peptide analogs containing (2-aminoethyl)phosphonic acid (ciliatine)
  作者：Kiyoshi Yamauchi、Souichi Ohtsuki、Masayoshi Kinoshita

  DOI：10.1021/jo00181a002

  日期：1984.4
• Yamauchi, Kiyoshi; Une, Fumiyoshi; Tabata, Sachio, Journal of the Chemical Society. Perkin transactions I, 1986, p. 765 - 770
  作者：Yamauchi, Kiyoshi、Une, Fumiyoshi、Tabata, Sachio、Kinoshita, Masayoshi

  DOI：——

  日期：——
• YAMAUCHI, KIYOSHI;UNE, FUMIYOSHI;TABATA, SACHIO;KINOSHITA, MASAYOSHI, J. CHEM. SOC. PERKIN TRANS., 1986, N 5, 765-770
  作者：YAMAUCHI, KIYOSHI、UNE, FUMIYOSHI、TABATA, SACHIO、KINOSHITA, MASAYOSHI

  DOI：——

  日期：——